(1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

Base Information

Chemical Name:(1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one
CAS No.:769122-49-8
Molecular Formula:C₃₀H₃₈O₁₀
Molecular Weight:558.626
Hs Code.:

(1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

Synonyms:(1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

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Chemical Property of (1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

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Technology Process of (1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

There total 11 articles about (1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 41.0%

: 769122-48-7
(1R,4aR,6aR,12bS)-1,3,4,4a,5,6,6a,12b-octahydro-1,4a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

: 79-21-0
peracetic acid

: (1R,4aR,6aR,12S,12aS,12bS)-12,12a-epoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-1,4a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

: 769122-49-8
(1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

Guidance literature:: In phosphate buffer; acetic acid; at 20 ℃; for 120h;
DOI:10.1016/j.tet.2004.06.059

Reference yield:

: 85679-49-8
2,4,4-trimethyl-3-vinyl-cyclohex-2-enone

: 769122-49-8
(1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: KOH; H₂ / RuCl₂[(R)-binap,(S,S)-DPEN] / propan-2-ol / 24 h / 20 °C / 6080 Torr

1.2: 11.6 g / DMAP / pyridine / 1.5 h / 20 °C

2.1: 99 percent / K₂CO₃ / methanol; CH₂Cl₂ / 2.5 h / 20 °C

3.1: 85 percent / DCC; DMAP / CH₂Cl₂ / 5 h / 20 °C

4.1: 35 percent / decane / 14 h / 180 °C

5.1: 77 percent / m-CPBA / CH₂Cl₂ / 24 h / 20 °C

6.1: 98 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / 1 h / 0 °C

7.1: 73 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 61 percent / L-proline / tetrahydrofuran / 14 h / 65 °C

9.1: 100 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

10.1: 71 percent / NaBH(OAc)3 / tetrahydrofuran / 15 h / 20 °C

11.1: 41 percent / aq. phosphate buffer; acetic acid / 120 h / 20 °C

With dmap; potassium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; tetrapropylammonium perruthennate; hydrogen; sodium tris(acetoxy)borohydride; potassium carbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; L-proline; [RuCl₂(R-BINAP)(S,S-DPEN)]; In tetrahydrofuran; methanol; phosphate buffer; decane; dichloromethane; acetic acid; isopropyl alcohol; 4.1: Diels-Akder reaction;
DOI:10.1016/j.tet.2004.06.059

Reference yield:

: 346688-12-8
(4aR,8S,8aS)-1-formyl-3,4,4a,5,6,7,8,8a-octahydro-4a,8-dihydroxy-2,5,5,8a-tetramethylnaphthalene

: 769122-49-8
(1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

Guidance literature:: Multi-step reaction with 4 steps

1: 61 percent / L-proline / tetrahydrofuran / 14 h / 65 °C

2: 100 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

3: 71 percent / NaBH(OAc)3 / tetrahydrofuran / 15 h / 20 °C

4: 41 percent / aq. phosphate buffer; acetic acid / 120 h / 20 °C

With tetrapropylammonium perruthennate; sodium tris(acetoxy)borohydride; 4-methylmorpholine N-oxide; L-proline; In tetrahydrofuran; phosphate buffer; dichloromethane; acetic acid;
DOI:10.1016/j.tet.2004.06.059